Pretty When You Obey

Pretty When You Obey

The Happiest Ending - Chapter 3

Chapter 3: The Promotion

Mistress Sara's avatar
Mistress Sara
Apr 24, 2026
∙ Paid

I woke to the soft rustle of fabric and the weight of satin against my skin.

The room was warm, oppressively warm, and the baby doll I’d been forced to sleep in clung to my body, slightly damp from sweat and something more shameful. My legs were bare, hairless, wrapped in sheets that smelled faintly of roses and powder. The silky thong between my cheeks had slipped during the night, riding up in a way that felt purposeful, mocking.

For a moment, I almost forgot where I was.

Then I sat up and the corset on the vanity, the dildo still resting on the pillow beside me, the pink glow of the vanity lights reminded me.

Not a dream. Not a joke.

I really did jerk off a stranger yesterday. I really did suck on a training dildo until my jaw ached.

And now I’m waking up in a staff bedroom, in a massage parlor where the masseuses wear high heels and customers pay for happy endings.

Except I’m not a masseuse. Not really.

I’m not like them. These women have their confidence and curves, their perfectly lined lips, their sense of ease in lace. I’m just a guy in panties, being taught how to pretend.

*A soft knock*

The door opened without waiting.

It was her—my trainer. Tight black pencil skirt, red nails, dark lipstick. Not a hair out of place. She looked like power in heels.

And next to her, cradled in one arm, was my new outfit.

“Morning, sunshine,” she said, far too cheery. “On your feet. First full shift starts soon.”

“Mmhm. Didn’t think you were just going to lay here being pretty, did you?”

She dropped the bundle of lace and straps onto the bed. A baby-blue corset. Sheer thigh-high stockings. A mesh thong so tiny it could be mistaken for a ribbon. Matching baby-blue heels—pointed toe, four-inch spike.

I hesitated.

She smiled.

“Aw. You wanted something a little more masculine?”

My cheeks flushed.

She stepped closer, picked up the thong with two fingers, and let it dangle in front of my face.

“Come on, sugar. You’ve already seen what women go through. All that massaging, stroking, teasing… You think it’s easy? It’s exhausting. Takes finesse. Takes charm. Takes control. You wanted to take advantage of a girl by not paying? Well, now you get to work like one.”

She let the thong fall into my lap.

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